Suzuki-Miyaura coupling (SMC) by palladium catalysts is promising C-C bond formation method with strong substrate adaptability and functional group tolerance, which has been applied in the synthesis of many natural substances and organic materials. It is well known that farnesene is one of the simplest acyclic sesquiterpenes derived from metabolic engineering via modified Saccharomyces cerevisiae, consisting of two isomers of α-farnesene and β-farnesene. Owning to the existence of conjugated double bonds in its molecular skeleton, β-farnesene has excellent performances with a broad spectrum of energy, agriculture and food industries. In this work, squalene was successfully produced using bio-based β-farnesene by homogeneous palladium-catalyzed SMC. Squalene is a chained triterpenoid compound with six isolated C=C bonds in molecular framework, which endows it unparalleled properties in medicine and industry. Subsequently, compared to catalytic activities of seven organic palladium, Pd(acac)2 exhibited the highest conversion and no by-products were detected. After optimization of reaction conditions, including catalyst amount, PPh3 amount, substance concentration, temperature and solvents, 99% of feedstock was triumphantly converted to squalene within 5 h and no side reactions occurred. Finally, crude products were purified by column chromatography on silica gel (petroleum ether/ethyl acetate=100v/1v) to obtain colorless transparent liquid. Given that harvest of squalene from sharks is unsustainable, that largely restricts extensive application of squalene. Therefore, it is of strategic importance to explore efficient synthetic route of squalene.

Suzuki-Miyaura coupling of bio-based β-farnesene by palladium catalysts: Factors affecting the efficient β-farnesene conversion and selectivity

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